Chemoenzymatic synthesis of novel 1,4-disubstituted 1,2,3-triazole derivatives from 2-heteroaryl substituted homopropargyl alcohols


BUYUKADALI N. N. , SEVEN S., ASLAN N., YENIDEDE D., Gumus A.

TETRAHEDRON-ASYMMETRY, vol.26, pp.1285-1291, 2015 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 26
  • Publication Date: 2015
  • Doi Number: 10.1016/j.tetasy.2015.10.001
  • Title of Journal : TETRAHEDRON-ASYMMETRY
  • Page Numbers: pp.1285-1291

Abstract

The one-pot synthesis of novel 1,4-disubstituted 1,2,3-triazoles from homopropargyl alcohol backbones is described. The key intermediates 2-benzothiophenyl la and 2-benzofuranyl lb substituted homopropargyl alcohols were synthesized starting from their corresponding carboxyaldehyde derivatives. The racemic heteroaryl-substituted homopropargyl alcohol derivatives are successfully resolved to give the corresponding enantiopure acetates and the alcohols with 84-99% ee by applying chemoenzymatic methods using various lipases. Enantiomerically enriched homopropargyl alcohol derivatives were reacted with various aromatic and aliphatic halides and sodium azide via a one-pot synthesis method and novel chiral benzothiophenyltriazoles 3a-9a and benzofuranyltriazoles 3b-9b were constructed without the isolation of potentially unstable organic azide intermediates. (C) 2015 Elsevier Ltd. All rights reserved.